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22232-71-9

22232-71-9

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22232-71-9 Usage

Chemical Properties

White Solid

Originator

Sanorex ,Sandoz ,US ,1973

Uses

Clinical trials as appetite depressant. Anorexic; CNS stimulant. Controlled substance (stimulant).

Manufacturing Process

Step 1: 1-(p-Chlorophenyl)-3-Ethoxy-11H-Isoindole - Crystalline triethyloxonium borontetrafluoride (21 g) (prepared from 23 g of borontrifluoride etherate and 11 g of epichlorohydrin) is dissolved in 100 ml of absolute methylenechloride. 3-(p-Chlorophenyl) phthalimidine (21 g) is added and the reaction mixture is stirred overnight at room temperature. The resulting solution is poured onto 50 ml of saturated sodium carbonate, extracted with 500 ml of ether and dried. Upon evaporation of the solvent there is obtained crude material which is recrystallized from methylene chloride/hexane (1:1) to yield 1-(p-chlorophenyl)-3-ethoxy-1H-isoindole; MP 102° to 103°C.Step 2: 5-(p-Chlorophenyl)-5-Hydroxy-2,3-Dihydro-5H-Imidazo[2,1- a]Isoindole - 1-(p-Chlorophenyl)-3-ethoxy-1H-isoindole (1 g), 2 g of ethyleneimine hydrotetrafluoroborate moistened with methylene chloride (containing approximately 0.66 g of dry salt) is refluxed in 25 ml of absolute toluene for 2 hours in an atmosphere of nitrogen. The resulting mixture is poured into 2 N sodium carbonate solution (25 ml) and extracted with ether. The ether solution is contacted with air for 6 days at room temperature to give the desired product. The crude material is recrystallized from acetone/hexane (1:1) to give 5-(p-chlorophenyl)-5-hydroxy-2,3-dihydro-5Himidazo[2,1-a]isoindole; MP 198° to 199°C.

Brand name

Mazanor (Wyeth); Sanorex (Novartis);Dasten;Degonon;Fagolipo;Lipese;Magrilan;Mazanor tablets;Mazeldene;Mazinil;Maznor;Tenorac.

Therapeutic Function

Antiobesity

World Health Organization (WHO)

Mazindol, an anorectic agent, was introduced into medicine in 1970 as an aid to weight reduction. It is controlled under Schedule IV of the 1971 Convention on Psychotropic Substances. It remains available in many countries with highly evolved drug regulatory authorities. (Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV), , , 1971)

Check Digit Verification of cas no

The CAS Registry Mumber 22232-71-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,2,3 and 2 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 22232-71:
(7*2)+(6*2)+(5*2)+(4*3)+(3*2)+(2*7)+(1*1)=69
69 % 10 = 9
So 22232-71-9 is a valid CAS Registry Number.
InChI:InChI=1/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2

22232-71-9Relevant articles and documents

Synthesis of halogenated analogs of 5-(4-chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo[2,1-a]-isoindole or mazindol for exploration of the dopamine transporter

Galinier,Garreau,Dognon,Ombetta-Goka,Frangin,Chalon,Besnard,Guilloteau

, p. 927 - 933 (1993)

In order to study the presynaptic dopamine transporter in the human brain by single photon emission tomography (SPET) or positron emission tomography (PET) we have developed new halogenated mazindol derivatives using a pathway involving a reaction between a dilithio derivative of 2-phenyl-2-imidazoline and appropriate methyl or ethyl halogenobenzoates. After HPLC purification and chemical characterization, the affinity for the dopamine transporter was studied in vitro with [3H]-GBR 12935 and compared to mazindol and nomifensine. Affinity potencies were determined as follows: mazindol > brominated derivatives > iodinated derivatives > nomifensine > fluorinated derivatives. The properties were related to the structure of these compounds and showed the importance of the nature of the substituent on the primary phenyl ring of mazindol for affinity to the dopamine transporter.

Mazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter

Houlihan, William J.,Kelly, Lawrence,Pankuch, Jessica,Koletar, Judith,Brand, Leonard,Janowsky, Aaron,Kopajtic, Theresa A.

, p. 4097 - 4109 (2007/10/03)

A series of mazindol (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [125I] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H → 5-OH) to mazindol on rat striatal membranes and HEK-hDAT cells. The 4′,7,8-trichloro analogue (38) of mazindol was the most potent and selective ligand for HEK-hDAT cells (DAT Ki = 1.1 nM; SERT/DAT = 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more tightly at the DAT than the corresponding keto tautomers.

Preparation of imidazo[2,1-a]isoindole compounds

-

, (2008/06/13)

The present invention relates to a process for the preparation of certain known imidazo[2,1-a]isoindoles of the general formula I: STR1 wherein X represents a hydrogen atom, a halogen atom or a lower alkoxy group. The said isoindoles, which may be prepared from novel lactams, have been shown to have utility as psychic energizers and anorectics.